Much like a captain of industry, a captain of "win"dustry excels at generating massive amounts of win like no one else's business, and/or amassing an immense amount of win over a long period of time. Such a person contributes greatly to the community at large by being awesome and detracting from the suckage and failure of others through their actions.

Chet: That dude just sunk five cups in a row in pong, made out with three chicks and talked the cops out of busting our party all while getting a Killtacular in Halo.